Sam Jacobs: Focus on problems during board meetings, not achievements

Sam Jacobs: Focus on problems during board meetings, not achievements

By OnBoard, by Passageways
15 November 2022
Partner Content

Pavilion Founder and CEO Sam Jacobs believes board members should use meeting time to discuss problems, not achievements. He explains why.

Most founders head into their first board meetings wearing rose-coloured glasses, ready to paint their company in the best light possible.

But seasoned CEOs and board members alike know board meetings are not sales meetings.

According to Sam Jacobs, founder and CEO of Pavilion (formerly known as Revenue Collective), a private membership for high-growth professionals, board meetings should veer toward pessimism rather than optimism. They are a place for 100 per cent honesty. They are an opportunity to lean into discomfort and learn from it.

Sam bootstrapped Pavilion to $10 million in ARR before securing a $25 million growth financing round led by Elephant Ventures and GTMfund in 2021. 

He’s learned a lot in the process, and he’s sharing his experience with OnBoard, by Passageways. These are his 7 tips for leading a productive boarding meeting—including why zeroing in on problem areas is worth your while. 

1. Know your numbers inside and out

As a CEO or founder preparing for a board meeting, your first task is deceptively simple: Know your facts. 

When you can’t easily answer questions, gloss over details, or can’t support your statements with numbers and examples, you’ll frustrate the board. 

“It’s OK to have your laptop open and have all your Salesforce dashboards out. You’ve got to have them up. And that’s why you should do dress rehearsals,” says Sam. 

If you can’t produce an answer on the spot, you’ll be asked to dig it up ASAP.  

When working on Pavilion’s new corporate business offering, Sam knew he would be asked what percentage of warm leads came from existing members. When the board meeting rolled around, he had the answer ready: 95 per cent. 

“The whole premise of the corporate businesses is that our community gives us warm leads into those companies that wouldn’t otherwise be there,” says Sam. 

“It turns out to be 95 per cent, so that’s good. It supports the hypothesis.” 

2. Avoid an Overly Positive Spin

It’s the fiduciary responsibility of any CEO to be honest about the business. It follows logically that the best way to be helpful in board meetings is to tell the truth. 

“The point of the meeting isn’t to put a bunch of spin on things and tell people things are going better than they actually are. Because inevitably the truth will come out anyway, and you’ll lose credibility,” Sam says.

Avoiding a positive spin can be a particularly hard lesson for VPs of sales and CROs who think their job is to act as cheerleaders focusing only on the upside.

The last thing you want to do is spin yourself or your CEO into a corner, where the end of the meeting leaves you breaking the news that your company is about to miss its projected numbers. It’s better to be straightforward from the start—even to the point of veering toward pessimism over optimism.

Just be ready to explain. 

“The main thing you have to be able to do is explain why what happened happened, and to forecast and predict the future,” Sam says.

The magic words that board members like to hear from a CEO are phrases like:

  • “As I presented three months ago…”
  • “If you remember from our previous meeting…”

These phrases show you are telling a continuous narrative and prove you are looking to the future in grounded, realistic ways. 

3. Use board decks to prioritise problems

Taking an honest approach means taking your problems out of the shadows and putting a spotlight on them during board meetings.

You need to learn how to quickly dig into what things are going poorly, and what’s being done to address them.  

Sam’s approach for his own board decks is to present an executive summary followed by departmental update slides. Those summaries included three slides:

  1. Department summary 
  2. Department challenges
  3. Department accomplishments

Sam has eliminated the accomplishments slide entirely.

“We’re not doing accomplishments anymore. We don’t need to. This is not about patting ourselves on the back. The accomplishments will be in the summary. We want to spend time focusing on what the problems are so that we can work on them,” Sam says.

To clarify, the point of this approach isn’t to be negative. It’s to be brutally honest and efficient during board meetings.

If you’re tempted to sugar-coat the facts because you’re fixated on your ability to raise money in the future, just remember that board decks are part of due diligence and if there are skeletons within your company, someone will discover them one way or another.

4. Listen actively—and answer questions carefully

If Sam has one pet peeve, it’s when a CEO doesn’t listen to questions from board members. When you don’t listen to questions, you can’t give a direct and honest answer.

“I’ve been in some board meetings where somebody on the board asks a question and the executive immediately begins nodding their head, thinking the vibe is to project confidence, optimism, and certainty when they didn’t really take the time to listen to the question,” Sam says.

When you don’t hear a question, you can’t answer it. That’s problematic for your board. 

When you are asked questions about numbers, remember the goal isn’t to hit a number. It’s to be able to explain why you hit the number. 

“We’re not looking for random volatility where one month we hit it and another month we don’t. We’re looking for predictability,” Sam says.

Questions about numbers should ideally include whether you hit them or not, why you hit them, and what number you expect to hit three months in the future.

5. Embrace feedback from outside the trenches

When you’re focused night and day on your company, it’s easy to get tunnel vision.

That’s why Sam says it can be valuable to listen to outside perspectives on your business—particularly from people who don’t spend much time on it. 

“There’s merit to dispassionate observers,” Sam says. 

“They don’t really care if you’ve been working on it for six months or 12 months or five years. They don’t have an emotional investment in confirming your ideas.”

If you’re a CEO, most of the time your executive team does have a lot of emotional investment. They want to support you by confirming your ideas. They want you to be on the right track. 

While unconditional support has a place in the business world, so does a reality check. 

At his latest board meeting, Sam confronted this truth head-on when a board member said the equivalent of: “Why are you doing X? Why don’t you just do Y?” 

Sam and his team had been working on the project in question for months. How did he respond? 

“I absorbed the feedback over the next 48 to 72 hours. And I was like, ‘You know what? They’re right.’ And I reallocated the resources of the executive team,” Sam said.

Don’t discount opinions just because the advice-giver doesn’t have the same battle scars you do. Advice from outside the trenches can be exactly what you need to gain a new perspective. 

6. Pursue board diversity with intention

There is currently an incredible appetite and interest in securing diverse board members. Sam says seeking diversity is important and should be done strategically.

“Like with anything related to diversity, you have to be intentional about it. It’s easy to say we’re going to hire the best candidate, but if you’re not looking in the right places and you’re not seeing diverse candidates, then you’re still just going to hire the person that is like everybody else,” he said.

If you only approach the white fraternity friends that you went to college with, you’re not going to find diverse board members. 

If you want diversity, you’ve got to go to places where you’re more likely to find diverse people and make sure they’re included in the evaluation process. That way, Sam says, you’ll have credibility when you say, “I just want to pick the best person.” 

7. Nail the secret to successful virtual board meetings

In-person board meetings are slowly coming back to life. While it’s nice to bring the team together in the same ZIP code, the problem with remote board meetings isn’t that you can’t shake hands. The problem is that they are chronically overscheduled. 

“The way it works in a virtual world is you’re back-to-back. The minute this meeting ends, the next meeting begins. And so there’s really no margin,” Sam says. 

When board meetings are in-person, they are typically an all-day affair. Even if the meeting itself doesn’t take an entire workday, the whole day is likely cleared to accommodate for attendee travel.

“When you’re on Zoom, the tendency of executive assistants and scheduling is you just keep putting meetings into any open spot. And then what happens is you just run out of time,” Sam says.

If you want virtual board meetings to be successful, you need to plan a time buffer in case meetings go longer than expected—and to give attendees breathing space afterward. 

There’s no doubt that remote board meetings are here to stay. That’s why OnBoard has created tools that provide clarity from initial meeting prep to final decision-making.

How to be a helpful board member

While CEOs and founders can find their marching orders above, what about board members themselves? 

It’s not enough to press “join Zoom meeting” and give the board several token hours of your time. If you really want to make a difference, Sam says there are several simple things to do:

  • Review the board deck in advance
  • Stay off your phone during the meeting
  • Be present and attentive
  • Apply lessons learned from other companies

“Sometimes VCs have so many other boards that they sit on that it’s hard for them to pay attention. And so my perspective would be if you’re going to be on the board, then give it your best,” Sam says.

If executives give you a homework assignment, such as an introduction they’d love to have, do your best to make it happen. For example, Sam had his board prepare a list of possible fundraising sources for Pavilion. 

Being a board member is a chance to lean in, put your resume of accomplishments to use, and help companies reach a level of excellence that will benefit everyone involved.  

OnBoard was designed to benefit CEOs and board members alike. To learn how we can transform your board meetings, schedule a demo and discover why 3,000+ global companies rely on our board intelligence platform. 

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